


Sex Ed

by CLeighWrites



Series: Wincest Big Bang 2019 [3]
Category: Supernatural
Genre: Dean Teaches Sam How to Jerk Off, Dean Winchester Has No Idea What He's Doing, Dean Winchester Has Self-Esteem Issues, Dean Winchester is Good With Children, Dean Winchester is Sam Winchester's Parent, Masturbation, POV Dean Winchester, Pubescence, Sam Winchester is Pubescent, Sex Education, Teenage Dean Winchester, Teenage Sam Winchester, Underage Masturbation, Weechesters, pre-wincest - Freeform
Language: English
Status: Completed
Published: 2020-01-23
Updated: 2020-01-23
Packaged: 2021-02-27 14:41:07
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 2,061
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22288801
Author URL: https://archiveofourown.org/users/CLeighWrites/pseuds/CLeighWrites
Summary: Dean promised Sammy that he would help him with some growing pains, which turns out to be a bit more than he’d bargained for.
Series: Wincest Big Bang 2019 [3]
Series URL: https://archiveofourown.org/series/1475429
Comments: 4
Kudos: 33





	Sex Ed

**Author's Note:**

> This will read fine by itself, but was written as a pre-prequel timestamp to my 2019 Wincest Big Bang, Love, Lies, & Lap Dances. It takes place about 3 years before Branching Out; Dean is 17 and Sammy is 13. It was so great writing my boys again!!
> 
> This was written for the SPN Fanfic Pond Unfic Challenge; my quote prompt was “I’m going to need you to put on some underwear before you say anything else." 
> 
> This also counts toward a square on my SPN Broment Bingo card - Asking for Advice
> 
>  **Warnings** \- weechesters, Dean feeling self-conscious about parenting, everything to do with jerking off, talking about it, thinking about it, instructions on how to do it, actually doing it… it’s all about self pleasure… there’s also some pseudo-not-okay-to-think-about-your-baby-brother-like-that thoughts, but no actual weecest
> 
>   
> 
> 
> Aesthetic gifted to me by [WinchesterWytch](https://archiveofourown.org/users/WinchesterWytch/pseuds/WinchesterWytch)!

“Dean,” Sammy drug out his name in a whine from the other side of the door. “You promised!” 

Dean could hear the desperation in his little brother’s voice. It was in the beginning stages of cracking and his begging was only exacerbating the change. Since John was out doing… whatever it was that he did when he’d ditch them, Dean had been the one Sammy had come home to to ask about his changing body and what is sex actually like, and all of those things newly teenaged boys ask. 

Of course, when Dean had turned thirteen, he got his own handgun, a crash course in how not to blow his own dick off, and a worn-out issue of playboy. He was told to take care of himself in the shower, to not hog the bathroom, and to _never_ get caught staring. Looking back on it, Dean’s surprised he’d managed to turn out the way he had. He’d make sure Sammy had a better education than he had gotten. And there was no way in hell Dean was letting Sam anywhere near a firearm. He was going to make sure his baby brother had as normal of a childhood as he was able. 

“Just a second, Sammy. Jesus.” He heard his brother shuffle away from the door with an unintelligible mumble.

Dean barely had time to shower by himself before Sammy got home from school. That morning the kid had blindsided him with questions about boners and what to do about them and how not to get them at the wrong times. Breakfast wasn’t exactly the time to have that conversation, and Dean honestly needed time to think about exactly how he was supposed to answer any of those questions to a thirteen-year-old kid, so he had promised that they would talk about it after school. Dean wasn’t even dry yet, and Sammy was already banging on the door waiting for his lesson in… whatever Dean was getting ready to teach him. 

After he’d toweled himself off good enough, he slipped his boxers on and opened the bathroom door. 

“Dean!?” 

Sammy was standing there in his t-shirt, pants gone, looking as stricken as a kid could look. When he straightened up, Dean couldn’t help but glance down and see that Sammy also wasn’t wearing any underwear and that the kid’s dick was hard and jutting out past the hem of his shirt. He was not going to be able to do this. _Why the fuck does dad have to be… dad?_

Dean cleared his throat and looked anywhere but the bottom of his fucking baby brother’s t-shirt. “I’m going to need you to put on some underwear before you say anything else."

“But, Dean!” Dean gave him a stern look, and Sam pouted. His lip honest to god quivered then he added, “It hurts to wear my underwear,” in a barely audible whisper.

Dean’s heart almost broke. Sammy was still so small for his age, he was still wearing the same tighty-whities he’d had for the last year or so. _Fuck, I’m going to need to get some money to get Sammy some boxers._ “It’s okay, Sammy. I know, boners fucking suck ass.” 

Dean ran his hand down his face to give himself time to think of what exactly he was supposed to do to help his little brother… without going to jail or some shit. He just had to think, when he was thirteen, what did he wish someone would have told him about this shit? 

“Alright, kiddo-”

“Dean,” Sammy whined. 

“Oh, right.” He kept forgetting that _Sam_ was too old now to be called ‘kiddo’. “Alright, Sammy. Why don’t we, um, sit on the couch.” 

Sam nodded and turned to walk toward the couch. Dean thought, belatedly, that maybe Sammy shouldn’t sit on that couch without anything between his skin and the fabric, he’d just have to make sure he had a good scrub down in the shower. Dean sat on the opposite side of the couch and turned himself to face his little brother, who sat in the same way, looking like Dean was about to solve all of his young life’s problems. 

“I don’t know what good I’m going to be here, Sammy.” Dean laughed. “Shit, when I was your age, dad just told me to jerk it in the shower, not to hog the bathroom, and to not get caught staring.” Dean rolled his eyes and Sammy just looked even more bewildered. 

“Staring at what?”

Dean hesitated for a second before deciding to be as blatantly honest as he could, it was for the kid’s own good. “Girls, boobs, asses; whatever catches your eye. Just make sure no one is watching you stare, and don’t stare too long; it’s creepy.”

Sam nodded and looked like he was memorizing everything Dean was saying like it was gospel. _That’s just what I need; no pressure._

“But what do I do…,” Sammy’s entire face flushed red as he looked down in his lap and tried to pull his shirt down to cover himself. 

Dean swallowed down his own embarrassment; him being embarrassed wasn’t going to help Sammy to not feel ashamed. After all, it wasn’t the kid’s fault, and he was going to be damned if he was going to be the one to give Sammy a complex about himself. 

“Okay, Sam. I’m just going to lay it out there. When you’re body is going through these changes, anything can, and will, get you hard. There’s nothing you can do about it.” Dean paused, as Sammy looked like he’d just been told that he had to streak through a pep rally. “It’s not all that bad, man.” 

Dean smiled and tried to lay a reassuring hand on Sam’s thigh, only to have him jerk away like he’d been burned. That’s when Dean remembered the kid was trying to get rid of his boner and wasn’t wearing any pants. 

“Alright, so first things first. We gotta get rid of _this_ , right?” Dean gestured to Sammy’s lap and he answered with a very enthusiastic nod accompanied with wide pleading puppy eyes. “Okay, so… oh, god. Have you ever, um…,” Dean shook his head, _just spit it out!_ “Have you ever played with yourself? Like in the shower, or when you’re in bed or anything?”

Sammy’s face turned even redder than before. “Yeah,” he looked down as he nodded and played with the hem of his shirt. 

“That’s okay, Sammy, that’s a good thing.”

Sam looked up at him equally pleased and apprehensive. “Really?”

“Yeah, that means that you know how to make yourself feel good. Right?”

“Yup.” He nodded again, then stopped, looking disappointed. “But, it doesn’t help, it just hurts more.”

“That’s because you’re probably not doing it quite right.” Dean took a deep breath, he had to help his little brother. “Why don’t you tell me how you usually do it, and I can try to help make it better for you.”

“Um, well… I um.” Sam’s hand inched its way up his thigh and he kept his head down. “It feels good when I grab it… and it’s really tender on the end.”

“Your head, yeah that’s a pretty standard sensitive spot.” Dean cleared his throat. “Do you rub it?” Dean couldn’t believe that this conversation was actually happening. 

Sam bit his lip and nodded his head, his hand creeping a little closer to his hip. “I do, but it still doesn’t help.”

“Okay, _how_ do you rub it?”

Sam raised his head and looked at Dean, his eyes full of fear and uncertainty. His fingers twitched under his shirt, and Dean knew what he needed to do. 

“If it’s easier for you to show me, that’s okay, Sammy. I know this is really uncomfortable… for both of us!” 

They both chuckled, but Sam nodded and let his plam go flat against his dick and he pushed down and away from himself. He made a little noise as he did it again, and Dean understood that he had literally been rubbing himself. 

“Is that all you do?” Sammy shook his head, and Dean pressed for more. “What else have you done?”

“Sometimes I, um….” instead of explaining it with words he demonstrated with his hand. 

Sam’s fingers curled around the head of his dick and gave it a squeeze a few times, then he removed his hand altogether. The poor kid was flushed to the tips of his ears and beyond the stretched out collar of his hand-me-down shirt. He refused to look at Dean, even as he tried to catch his attention. 

“Sammy, you don’t have to be embarrassed with me. I’m your brother, okay? You’re not doing anything wrong.” He shook his head and sniffled. _Great, now he’s crying._ “Sam, you’re killing me, man. Look at me.” 

He sniffled again and turned his face toward Dean. His eyes were glistening, the skin surrounding them was red and puffy, not from blushing; he was breaking Dean’s heart, no wonder the kid was so anxious for Dean to help him. 

“I’m going to help you, okay, Sammy?” 

_Sniffle_ , “okay.” He nodded. “What am I doing wrong?” His voice cracked and pitched on the last word.

Dean let out a breath. “You’re not doing anything _wrong_. Both of those things can feel really good, but just not by themselves. Have you ever moved your hand while you’re holding it? Sort of combine both of those things together.”

Sam’s brow furrowed, but at Dean’s nod, he tentatively reached back into his lap and grabbed himself. He gave his dick a little squeeze then stroked, and his breath hitched. He moved his hand back down to the base, then stroked himself again and moaned. 

“Oh, Dean….” Sammy had a smile on his face and he experimentally tried flicking his wrist and twisting around his head.

Dean knew he wasn’t saying his name out of some imagined fantasy, he was just thankful that Dean had shown him how to jerk off properly. But that little moan of his name coming from his little brother’s lips had Dean starting to stiffen himself. _You are seventeen, get a grip!_

“Alright, alright. Enough of that. Don’t go moaning my name while you’re jacking off.” Dean smirked to lessen the sting of his aggressive tone, but he had to do something to bring this whole thing to an end before… well, just _before_. “You think you’ve got the hang of it now?”

Sam took his hand off of his dick and pulled his shirt back down. “Yeah.”

“And some kind of lube won’t hurt either, trust me, you do not want to chaffe yourself down there, dude. Not cool.” Dean shook his head in experienced resignation. 

Sammy nodded again. “Lube. Like oil?” 

“Yeah.” Then Dean realized Sammy was probably referencing their recent oil change lesson with Baby, and shook his head. “No, not like _motor_ oil. That’s a completely different kind of lube. Like, lotion and smooth shit that’s supposed to go on skin. In a pinch, you can even use conditioner, if you’re in the shower or something.” Dean shrugged like it was no big deal. _That’s that_. 

Sam jumped when Dean clapped his hands together and stood from the couch. “Okay, so, uh… you wanna hop in the shower now?” Dean raised and wiggled his eyebrows.

“Oh my god, Dean.” Sammy rolled his eyes. _There’s my annoying little brother._ “Yeah, I guess so. What’s for dinner?”

“Mac ‘n’ cheese?”

“With hot dogs and ketchup!?”

“Sure thing, little brother.” 

Sam rushed at him and wrapped his arms around his waist. Dean slung an arm around his shoulders and gave him a small squeeze. 

“Thanks, De.”

“No problem, Sammy… now go ‘walk your dog’, and let me cook dinner.”

“Dean,” Sam lamented, but turned and went into the bathroom. 

As soon as the door clicked shut, Dean palmed himself through his boxers and debated rubbing one off really quick, or just ignoring it till after Sammy went to bed. _There’s no way you jerk off from teaching your baby brother to jerk off, just ignore it._

After Sammy came out of the bathroom, flushed and smiling, Dean barely made it through dinner and an episode each of _Hercules_ and _Xena: Warrior Princess_ , before Sam went to bed and Dean was able to hog the bathroom uninterrupted.

**Author's Note:**

> Thanks for reading! Don't be shy, let me know what you think!


End file.
